


Illicit Daydreams pt 2

by CLeighWrites



Series: Illicit Daydreams [2]
Category: Supernatural
Genre: Aftercare, Anal Fingering, Anal Plug, Anal Sex, Bottom Dean Winchester/Top Sam Winchester, Brother/Brother Incest, Dean Winchester & Sam Winchester Cuddling, Dean Winchester Gives Oral Sex, Dom Sam Winchester, Dom/sub, Double Penetration, Double Penetration in Two Holes, Established Dean Winchester/Sam Winchester, Established Relationship, F/M, Incest, M/M, Masturbation, Multiple Orgasms, Naked Cuddling, Oral Sex, Orgasm Control, Orgasm Delay, Sex Toys, Sibling Incest, Simultaneous Orgasm, Stripping, Sub Dean Winchester, Supernatural Kink Bingo 2019, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex, Voyeurism, sub Reader
Language: English
Status: Completed
Published: 2019-04-19
Updated: 2019-04-19
Packaged: 2020-01-16 14:29:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,507
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18523450
Author URL: https://archiveofourown.org/users/CLeighWrites/pseuds/CLeighWrites
Summary: After getting picked up by two very tall, very handsome brothers while celebrating, you head back to their motel room to live out one of your darkest fantasies.





	Illicit Daydreams pt 2

Sam flicked the lights on and you saw Dean sitting on the foot of the king size bed removing his shoes. Sam came up behind you and slipped his hands down your arms, then around your middle and played at the waistband of your pants, teasing the tender skin of your stomach. He rested his head on yours and slipped his fingers under your jeans. 

“Y/N,” Sam’s voice broke through your haze. 

“Hmm?” You swayed on your feet, but he held you steady. 

“Baby girl, you got a safeword?” His hand sank lower into your pants. 

“Uh huh.” Your eyes were on Dean now, stripping in front of the two of you. 

“I need to hear it, Y/N. What’s your safeword?” His voice was hard and his fingers stilled before they got to where you needed them.

You closed your eyes as Dean slid his pants and boxers down to the floor. Shaking your head you tried to pull your safeword to the forefront of your mind. It had been a while since it was necessary. “It’s...um, pineapple.” When you opened your eyes again Dean was naked on his knees in front of you, hands behind his back, his eyes cast downward.

“De, your safeword?” Sam’s fingers started to trace their way down to your clit, slowly caressing your smooth skin.

Dean’s eyes remained on the floor at your feet when he answered, “Lawrence.”

“That’s right.” Sam’s fingers crooked and dipped into your cunt before he asked, “You got any hard limits?”

“Mmm, yeah. Um….” It was hard for you to think with Sam’s fingers gently pumping in and out of you. “Choking.”

“No choking. Got it. Anything else?”

“Yeah, watersports, scat play.”

“So, none of that. Is that all?”

“I’ve never done blood play?”

Sam stiffened behind you and Dean shifted in his place. “We don’t do blood play,” Sam responded. 

“Okay, I’m sorry.”

Sam removed his hand from your pants and turned you to face him. “No need to apologize, you’ve done nothing wrong.” He smiled down at you, “Now, rules. Clearly, I am in charge. Dean is under my full control. He does nothing unless I tell him to. I don’t expect you to submit fully; like you said, we don’t know each other.” He laughed a little, and you let out a nervous giggle. “We’re just going to play and have fun. We want you to feel comfortable with us; what would you like to do?”

Your face flushed as you thought about what you really wanted, it obviously wasn’t going to be an issue for the brothers. “I um… I really would like to, I mean, I’ve always been curious about….” You ducked your chin down to your chest, embarrassed to say what you really wanted, even given your current circumstance. 

“Y/N, you don’t need to be embarrassed, we’re very open.”

“I just- I want to see the two of you… together.”

Sam chuckled, “To be honest, that’s not what I was expecting. That’s totally doable. Anything else?”

“I’d also like to be between the two of you. Have you both use me.”

“Also doable. Have you ever worn a butt plug before?”

You grinned at your memories of when your last dom had anal trained you. “Yes, Sir.” 

“Good girl.” Sam leaned down and placed his lips to yours and slid his hands up your shirt. “De?” Sam asked as he slid your shirt up and over your head.

“Yes, Sir?” 

“Go to our bag and get Y/N the new plug we got the other day and the lube.”

“Yes, Sir.” 

You heard Dean stand, take a few steps, and then a zipper. Sam had completely removed your top and bra and was fondling your breasts with his left hand as his right flitted down your stomach to undo the button of your jeans. Your stomach clenched when his knuckles scraped your skin as he lowered your pants and underwear down over the curves of your hips. Dean stepped up beside you, kneeled and held out his hands to show Sam the plug and bottle of lube. 

Sam tossed your tops to the floor beside the bed and placed his hand on the side of Dean’s face. You watched as Dean leaned into the touch, closing his eyes. The love and the trust that went into that touch broke your heart; you could only hope to have a connection like that with someone one day.

“Thank you, De.” 

“Yes, Sir.”

Sam took the toy and lube from his brother and smiled at you, “De, why don’t you make our girl here feel good? Take her to the bed.”

“Yes, Sir.”

Dean reached for your hand and you stepped out of the pool of clothing at your feet as you allowed him to lead you to the bed. You glanced nervously over your shoulder and caught sight of Sam removing his shirt. His arms above his head and his gloriously toned torso, muscles stretched out, on full display. Your attention was brought back to Dean when he grabbed your hips to turn you to face him before he sat you on the bed. The sound of Sam’s zipper was pushed from your mind as Dean leaned down to kiss you, gently guiding you to lie down under him, as you opened up to him; lips and legs parting to accommodate him. 

Dean’s skin was smooth under your fingers as you ran your hands along his back and shoulders, hard muscles under soft skin. His tongue made its way through your lips to dance with yours. As his mouth moved down to your neck, his fingers traced their way up your side to your breast. His hand nearly as big as his brothers, covering the entire orb, his nimble fingers raising your nipple to a hard peak in seconds. His lips replaced his fingers as his other hand worked your other breast, then switched places with his mouth once again. 

Your hands found their way to the short hairs on the back of his head as his lips and teeth and tongue alternated between your swollen nipples. You threw your head back into the mattress when his free hand worked its way between your bodies and two of his fingers surrounded your clit, applying the most torturously gentle pressure there. Your body undulated beneath him, trying to gain more friction, make him work at you harder than he was. 

“Mmm, please… more,” you begged.

“De.” At the sound of Sam’s voice, Dean stopped and sat up on the bed, resuming the position he had taken on the floor. 

You were left, heaving and cold, spread out on the mattress. Sam’s heated gaze made you clench around nothing as his eyes traveled over your body before doing the same to his brother. Having assessed the situation he seemed to make up his mind and opened the lube, pouring a liberal amount onto his fingers. 

“De.” 

“Yes, Sir?” He was poised, but still breathing heavily. You could only imagine the control it was taking him to hold himself so still.

“I want you to bend over and let me prep you while you devour Y/N’s pussy. I want her to come on your mouth while I open you up for me.”

“Yes, Sir.” The neediness in Dean’s voice made your pulse race. You couldn’t believe that you were going to be a part of this; these two gorgeous brothers being with each other in this way. It was clear how much they loved one another. The way they would look at or touch or speak to the other. It was beautiful; they were beautiful. 

All such awe was thrown from your mind once Dean’s tongue slid through your soaked folds. He hummed at the taste of you and swirled his tongue around your clit. Your hands flew to your breasts, grasping and pulling at your nipples while he feasted on your womanhood. 

You were barely able to watch as Sam crawled up the bed behind his brother and delicately ran his fingers down the older man’s spine with his clean hand. “So good for me, De. Make her scream your name, show her how good you are for me.” Sam’s other hand must have made contact with him then because Dean rocked back and moaned into your cunt. 

Dean could win a gold medal at the Olympics for the oral gymnastics he was performing on your soaked sex. You couldn’t even keep track of everything he was doing. As soon as he would get the desired reaction from you he would switch things up and attack you in a different way. You could tell whenever Sam would hit a particularly sensitive spot in Dean because his mouth would go a little slacker and he would moan into you and send those deliciously deep vibrations through your entire body. 

“She’s so close, De,” Sam cooed, “Get her ready for us.”

Dean took his cue from his brother and deftly slid two of his thick digits into your slick cunt, quickly finding your sweet spot, while his little finger worked its way into your tighter hole, his spit and your juices making the stretch bearable. He began a brutally quick pace on your clit with his tongue as his fingers fucked you hard and fast. When your walls started to greedily suck at his fingers he closed his lips around your clit and shook his face, humming into you like you were the most delicious thing he’d ever consumed. You came instantly, screaming his name and clawing at your own hair, your body refusing to let his fingers slide free. 

“So fucking sexy when you come, baby girl. Good boy, De, now plug her up.” Sam thread his fingers through Dean’s hair and pulled his head back, exposing his flushed throat to you. He slid the buttplug into Dean’s mouth so that the lubed plug end was facing you. 

Dean preened at the praise, looking down at you with lust-hazed eyes. He looked like he couldn’t tell you his name, let alone where he was or what day it was. You weren’t quite there yet, but you could tell that you were on your way there. Dean’s head dipped back down between your legs, his hands scooping up under your ass, raising you up to him as he set the plug at your pucker. You could feel the resistance so you relaxed and opened up for him to push the plug past that tight ring of muscle. Dean shoved with his mouth until the plug was set in place, then kissed your thigh as he righted himself. The familiar fullness made you clench around the plug.

“Sit back Y/N. Get comfortable on the pillows and spread those legs for us. You can play with yourself if you want to.” Sam’s smirk made your stomach muscles seize. 

Sam placed his wide palm between Dean’s shoulders and bent him over, face to the mattress, ass in the air. Dean whined when Sam removed his fingers from his ass and instinctively rocked backward, trying to find them again. Sam slapped his right buttock hard, shoving Dean further into the mattress as he cried out. 

“I’m sorry, Sir,” Dean mumbled into the bedspread. 

“I should make you wait for it, now, but we’ve got company. Be good, or you don’t get to come tonight, De,” Sam whispered into his brother’s ear, but his eyes were glued to yours. 

Dean whimpered but didn’t move when Sam pulled himself away from his back. Sam grabbed the bottle of lube and stroked himself slick from base to tip. You watched his long fingers expertly distribute the shiny substance over his length and girth. Your mouth watered at the sight, wanting nothing more but to have his cock in your mouth. Sam smirked as you licked your lips and moaned when he lined himself up behind Dean. 

Your eyes widened and you looked from Dean back to Sam, who winked at you before pressing his hips flush to his brother’s ass. You couldn’t believe your eyes; everything you had ever fantasized about was playing out right in front of you. Mere inches away from you, two brothers, who were clearly in love with each other, were affirming their love in the most intimate way possible. You were overcome with emotion and could feel a tear slip down your cheek as you watched Sam slip deeper into his brother. Dean sighed and smiled into the bedspread. 

Your fingers traced their way down your torso as you watched the two men, attuned to each of their movements. The way Sam would shake the hair out of his face, fingers digging into the flesh of Dean’s hips, and the way Dean would cling to the bedspread, white knuckling the fabric with both fists clenched and eyes screwed shut in ecstasy. The sound of Sam’s grunts and Dean’s moans reverberated through the mattress and went straight to your core, reigniting the embers as your fingers finally found your aching bud. 

“So good for me, De,” Sam groaned before he slowed his pace. He leaned over Dean’s back, kissing him softly behind his ear, and Dean leaned into the touch. “We can’t leave Y/N out though. You wanna get your dick wet, big brother?”

Your clit throbbed at his words and you eagerly got to your knees, waiting to be told how Sam wanted you. He laughed at your enthusiasm, sliding himself out of his brother and stepping away from the bed. Dean breathed out a contented breath and let his legs fall flat so that he was lying face down across the bed, his feet hanging over the edge. Sam went to a duffel bag and you heard the sound of foil wrappers being ripped before he turned back toward the bed. 

Sam threw something toward you on the bed and motioned for you to pick it up. “Roll over, Dean, so she can get you ready for her.” 

Dean mumbled something incoherent then used his arms to roll himself over. You grabbed the condom and ripped it open, removing the thin contraceptive from the wrapper and pinched the tip of it between your fingers. You looked at Sam before you grabbed Dean, and after getting his nod of approval you wrapped your fingers around his base and positioned the condom on his flushed head. Dean hissed at the cool feeling of the spermicide as you gripped tight and unrolled the sheathing over his sensitive cock. He was heavy in your hand and throbbed as you smoothed the condom down over him. 

You noticed that Sam had already put a condom on, and had lubed himself up when he leaned over to dribble some lube onto the tip of Dean’s cock. Dean closed his eyes and hissed in a breath when you followed the trickling liquid with your fingers, making sure he was well lubricated. Unable to resist, you leaned down and kitten licked Dean’s hip bone, giving him kisses up his abdomen until you reached his nipple. Dean made the most amazing noises, and you were proud to have elicited some yourself. 

Hearing him clear his throat, your eyes shot up to find Sam eyeing you hungrily, his hand firmly holding the base of his cock. “Hop on, baby girl. I’ll be right behind you.”

Your inner walls clenched around nothing at his promise, and your arousal grew tenfold when the action caused the plug in your ass to shift as well. Since you were already almost in position, you were able to follow Sam’s command quickly, throwing your leg over Dean’s hips and angling yourself over him. 

“Time to get your dick wet, big brother. Wait for me before you fuck her.” 

Dean’s hands made their way up your legs before settling on your hips. You reached between you to position his cockhead at your entrance, and you took in a settling breath as you sank down onto him. Dean’s deep groan resonated within you and you gripped his arms tighter to keep from collapsing on top of him. Sam’s hand on your body brought you back to your current situation, while also reminding you of what was about to happen. You had been gifted the opportunity to participate in an incestual relationship, and you wanted to be able to remember all of it. 

Sam’s fingers traced their way down your back as you took Dean’s cock in until your pelvises touched. You tried to remain still, knowing that Sam wanted them to start fucking you at the same time. Dean’s fingers were flexing and rubbing in place at your hips, waiting for the word from his brother to move. When Sam’s hand got to the rounded curve of your ass, he added his other hand to the other cheek and gave both sides a firm squeeze. He spread you open and hummed at what he saw. 

“Oh, baby girl. You are gorgeous. Your little hole all stretched out, waiting for me. De, you should see her, she’s dripping around your cock. So pretty.” 

You felt Dean’s dick twitch inside you, but otherwise, he didn’t move a muscle. You felt amazing pressure inside of you as Sam pushed the plug in deeper and began to fuck you with it. The sensation also caused Dean’s grip on your hips to harden, and a moan to escape both of you. 

“It’s so nice to have two cock sluts to play with. I wonder who I can get to come first,” Sam mused as he continued to work your hole open wider. 

After a few moments, you weren’t able to hold yourself up anymore and had lowered yourself to your elbows, resting your body on top of Dean’s. His breathing was getting heavier, along with yours, causing an oceanic feeling to come over you. Your mind was reeling, and your body was thrumming with pent up energy as you drifted between the brothers.

Sam’s teeth biting into the flesh of your ass pulled you from your sea of thoughts just in time for him to finally remove the plug from its place. You whined at the sudden loss, but it turned into a moan as Sam sunk in three lubed fingers and instantly began to scissor them. You were grateful that he was taking his time opening you up. It had been a while since you had done anal play and Sam was impressively girthy. You would have been lying if you had said that you weren’t a little bit concerned about him actually wrecking your ass. 

“You’re just about ready for me, baby girl. We’re going to wreck both of your tight little holes; you’re going to be ruined for any other men after this.”

You arched your back and rocked back onto both men and begged, “Yes, please!”

Sam shoved his fingers in deep, but made them as small as possible, “Please, what?”

“Please, Sir,” you corrected yourself, your ass reflexively sucking at his fingers. 

“That’s it, baby girl. You ready, De? Gonna fuck her hard for me, big brother?” You clenched around both of them at the epithet. “Oh, De, she really likes it when I call you ‘big brother.’ What about when you call me by my nickname?”

You felt Sam’s other hand slip underneath you, then Dean’s hips jerked forward, “Oh yes, baby boy.” You couldn’t help having the same reaction, nor the moan that slipped through your lips. 

“Oh yeah, she likes that a lot. We might have to keep this one, De.”

You shivered at the implication, but you didn’t feel at all in danger; somehow knowing that it was just talk. Getting the same feeling you had gotten at the bar, there was just something about both of these men that made you trust them. 

Sam gave your ass a hard smack as he removed his fingers, wiping them off on the cheap motel bedspread, then you felt the bed depress as he settled his knees on either side of Dean’s legs, but on the inside of yours, causing your legs to spread out even wider. You were now solidly laying on top of Dean, and you could feel the brothers’ fingers entwine on your hip as they both held onto you while Sam lined himself up, ready to join Dean inside of you. 

You felt the burn of your muscles as Sam slowly started to shove in. You breathed in and out deeply, both relaxing your muscles as well as focusing on pulling Sam in deeper. Dean’s hand that wasn’t tangled with Sam’s made its way up your back, under your arm and held you to him. The feeling of complete fullness was invading all of your senses and you began to let yourself fully go, giving yourself over to these brothers to do with you what they would. 

Sam dribbled more lube directly onto your open hole as he continued to sink further into you. The coolness of the liquid, added to the heat of Sam’s thinly covered flesh on yours, made for a shocking new sensation; coupled with Dean’s pulsing cock settled deep into your core, you were the very definition of overstimulated, speared between these two great men. After a few more moments of delicious teasing, Sam was fully engulfed in your tight heat.

Sam’s hand tightened around Dean’s on your hip. “Alright, De, she’s ready for us. You ready to fuck her, big brother?” Sam chuckled when you gasped at the fullness you felt this time when you tightened around both of them. 

“Yes, Sir.”

“I’m your baby boy now, De,” Sam reprimanded, and Dean’s dick twitched inside of you again.

“Yes, baby boy. I’m ready.” 

Your face was buried in Dean’s shoulder, so you didn’t see them exchange a look, and you didn’t feel them signal each other physically, but they both pulled back before plunging back into you at the same time. They set a steady pace, not too fast, but still quick enough for you to have trouble keeping your breath. Sam’s grunts behind you, and Dean’s beneath you, mixed with your own incoherent moans of pleasure as they fucked into you. For the most part, they stayed in sync, both sliding in and out of you at the same time, their cocks coming together on opposite sides of the thin wall of muscles between them. They were fucking each other through you. That thought alone was enough to send you over the edge. 

“Come for us, baby girl. You can come as many times as you need to. Show us how much you want us.” The words were pounded into you by both men, and before Sam was even finished speaking you were squeezing them both tight and screaming out your release. 

Neither brother let up from his assault on you. Fucking you hard through your string of orgasms, neither your breathing nor body had time to regulate before another wave of pleasure rolled through you. You were seeing stars and were fighting for breath when one of the men found your clit. He started rubbing hard circles over the sensitive bundle, and Dean bit into your neck while someone grabbed the hair on the back of your head causing you to come undone again. 

The brothers slowed their pace slightly and Sam leaned down over you, “I’m close, come with me, big brother.” 

You whimpered and Dean nodded while Sam straightened up behind you. This time when they started to fuck you, there was no gradual build-up, they each thrust into you at a dizzying speed, fucking you into one another. The ebb and flow of them were too much to handle and you gushed out one final explosive orgasm just before both men settled in deep. You felt both of them as they pulsed into you, grunting above and below you.

Completely and utterly spent, you collapsed on top of Dean, unable to move your body at all as you tried to regulate your breathing. Sam was able to hold himself over you and his brother, but his arms were shaky as he bent down to suckle at your neck. You laughed as he hit a particularly sensitive spot and you could feel his responding grin. You both hissed as he slid out of you and stood. Dean was just as gone as you were, and neither of you moved to separate yourselves. 

A cool cloth on your ass made you jump and Dean’s slightly softened cock slide out from you. Sam had gotten wet wash clothes to clean you with. His touch was gentle as he wiped away the mix of your arousal and the lubricant from between your legs. You were overly sensitive, but the cool rag helped to alleviate some of the discomfort. Dean’s arms were still around you when Sam playfully slapped your ass to get you to roll onto your side and off of his brother. He was just as gentle as he removed the condom and used a second cloth to clean him off just as thoroughly. 

The way you rolled had one of Dean’s arms trapped under your shoulder, but he didn’t try to take it back, instead, he curled his fingers around your shoulder and mindlessly traced patterns into your skin as he was cleaned off. When Sam was finished Dean rolled over to face you and tucked his head under your chin. You wrapped him in your arms and ran your fingers through his hair. It was soothing to be wrapped up in each other, comforting one another right now. You needed the physical contact, and it seemed that Dean needed it even more than you did. 

When Sam stepped back into your line of vision he was in boxer briefs and grabbed a blanket from somewhere, then shut off the light. You felt a rush of air, then the soft material covered both Dean’s and your bodies. You felt a tap on your leg and a gentle shove as Sam worked with you to scoot yourself and Dean more toward the center of the bed, then Sam settled in behind his brother. 

You heard more than saw Sam kiss Dean’s forehead, then fingers were in your hair as Sam guided you to kiss him as well. “Thank you, Y/N.”

You laughed, “Please, I should be thanking you guys. I’m surprised I didn’t pass out. I’ve never come so hard in my life!”

Sam and Dean both chuckled at that, “Pleasure to be of service,” Dean joked sleepily. 

You snuggled down deeper into the bed and Dean’s embrace, the fog of sleep creeping into your consciousness. Sam found his place curled up into his brother, hand draped across him and you. That feeling of safety found you again along with one of contentment. You quickly drifted off into the deepest sleep you’d had in years, in the arms of these breathtakingly beautiful strangers.

**Author's Note:**

> Thanks for reading! Don't be shy, let me know what you think!


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